Tracing the Antibacterial Performance of Bis-Imidazolium-based Ionic Liquid Derivatives

Ionic liquid (IL) cationic species have recently captivated the attention of pharmacists, biochemists, and biomedical scientists as promising antibacterial agents to deal with the multidrug resistance bacteria crisis. The structure and functional groups of ILs influence their physiochemical properties and biological activities. However, a comprehensive study is required to fully understand the details of the antibacterial activity of ILs carrying various functional groups. Herein, dicationic ILs (DCILs) are reported based on imidazolium rings as efficient antibacterial agents. The DCILs carried various functionalities such as 2-hydroxybutyl (DCIL-1), 2-hydroxy-3-isopropoxypropyl (DCIL-2), 2-hydroxy-3-(methacryloyloxy)propyl (DCIL-3), 2-hydroxy-2-phenylethyl (DCIL-4), and 2-hydroxy-3-phenoxypropyl (DCIL-5). The structure-antibacterial activity relationships of the DCILs against Gram-positive (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) were comprehensively studied through antibacterial tests, morphology analysis, and adhesion tests. The experimental assays revealed an antibacterial efficacy order of DCIL-5 > DCIL-1 > DCIL-4 > DCIL-2 > DCIL-3. The all-atom molecular dynamics (MD) simulation showed a deep permeation of the hydrophobic −OPh functional group of DCIL-5 through the E. coli membrane model in agreement with the experimental observations. Current findings assist scientists in designing new task-specific DCILs for effective interactions with biological membranes for different applications.